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US3658819A - 3-(2'-tetrahydropyranyl) - 1 2 3 4 6 7-hexahydro - 5h - cyclopentapyrimidine-2 4-dione - Google Patents

3-(2'-tetrahydropyranyl) - 1 2 3 4 6 7-hexahydro - 5h - cyclopentapyrimidine-2 4-dione Download PDF

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US3658819A
US3658819A US3499A US3658819DA US3658819A US 3658819 A US3658819 A US 3658819A US 3499 A US3499 A US 3499A US 3658819D A US3658819D A US 3658819DA US 3658819 A US3658819 A US 3658819A
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tetrahydropyranyl
compound
cyclopentapyrimidine
dione
urea
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Daniel Bertin
Jacques Perronnet
Andre Teche
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Sanofi Aventis France
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Roussel Uclaf SA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/14—Nitrogen atoms not forming part of a nitro radical

Definitions

  • compositions containing the same, process and method are provided.
  • the compound I possesses pesticidal, particularly herbicidal properties.
  • the compound of Formula I is endowed with remarkable pesticidal, specifically herbicidal properties which 3,658,819 Patented Apr. 25, 1972 make it useful in agriculture for controlling harmful organisms and more particularly for controlling the growth of weeds.
  • the process of the invention for the preparation of compound I comprises condensing 2-ethoxycarbonyl-cyclopentanone with N-(Z-tetrahydropyranyl)-urea in the presence of a proton donor, cyclizing the resulting N-(2-tetrahydropyranyl)-N-(2-ethoxycarbonyl) 1 cyclopentenylurea in the presence of a basic agent, and recovering the desired compound of Formula I.
  • the proton donor is an acid, such as phos phoric acid, acetic acid, pyruvic acid, an ammonium salt such as ammonium chloride, or an acidic ion exchange resin.
  • an acid such as phos phoric acid, acetic acid, pyruvic acid, an ammonium salt such as ammonium chloride, or an acidic ion exchange resin.
  • the condensation of 2-ethoxycarbonyl-cyclopentanone with N-(Z-tetrahydropyranyl)-urea is preferably carried out in an organic polar solvent such as acetonitrile, nitrobenzene, nitromethane or dimethylsulfoxide.
  • the basic agent used in the cyclization reaction is preferably an alkali-metal alcoholate such as an alkali-metal alkoxide, e.g. sodium or potassium, methylate or ethylate, and the cyclization reaction is performed in the presence of an alcohol such as ethanol; or the basic agent is an alkali-metal amide such as sodium or potassium amide, or an alkali-metal hydride, such as sodium hydride, and the cyclization reaction is performed in an ether such as tetrahydrofuran, ethyl ether, or in dimethylformamide.
  • an alkali-metal alcoholate such as an alkali-metal alkoxide, e.g. sodium or potassium, methylate or ethylate
  • an alcohol such as ethanol
  • the basic agent is an alkali-metal amide such as sodium or potassium amide, or an alkali-metal hydride, such as sodium hydride, and the cyclization reaction is performed
  • the pesticidal, specifically herbicidal compositions of the invention generally, contain from 10 to by weight of the compound I as active ingredient, and an adjuvant. These compositions may also contain one or several other pesticidal agents or one or several products influencing plant growth.
  • compositions of the invention contain from 10 to 50% by weight of active ingredient.
  • compositions of the invention can be in the form of powders, granules, suspensions, emulsions, solutions containing specifically, in addition to the active principles, an adjuvant, such as a surface-active cationic, anionic or non-ionic agent, such as aryl or alkylarylsulfonates, inert powders such as talc, clays, silicates, colloidal kaolin, kieselguhr, synthetic silica, and the like, and/or a vehicle such as water, alcohol, hydrocarbons or other organic solvents, a mineral, animal or vegetable oil, etc.
  • an adjuvant such as a surface-active cationic, anionic or non-ionic agent, such as aryl or alkylarylsulfonates, inert powders such as talc, clays, silicates, colloidal kaolin, kieselguhr, synthetic silica, and the like
  • a vehicle such as water, alcohol, hydrocarbons or other organic solvents,
  • the invention likewise relates to a method of pesticidal control.
  • Said method is more particularly a method of controlling the growth of harmful organisms and specifically of weeds, which comprises contacting the harmful organisms, particularly the weeds and/or their seeds, with a pesticidal amount, particularly a herbicidal amount of the compound I.
  • the compound of Formula I is preferably applied in the form of the compositions described above.
  • compositions of the invention are applied at doses sufiicient to exert their pesticidal, specifically herbicidal activities.
  • doses of active ingredient to be applied may vary as a function of the weeds, the nature of the ground and the weather conditions.
  • the invention also relates to N-(2-tetrahydropyranyl)- N'- .(2-ethoxycarbonyl)-1-cyclopentenyl-urea which is an intermediate in the process described above.
  • N-(Z-tetrahydropyranyl)-urea takes the reaction mixture to reflux, keeps it at reflux for two hours, while removing the water formed during the reaction by azeotropic distillation and simultaneously adding benzene to keep the volume constant.
  • One then adds 25 g. of N-(Z-tetrahydropyranyl)-urea continues distillation with addition of benzene for two hours, again adds 25 g. of N-(Z-tetrahydropyranyl)-urea and keeps at reflux with distillation and addition of benzene for two more hours.
  • STAGE B 3(2-TETRAHYDROPYRANYL)-1,2,3,4,6,7 5H- CYCLOPENTAPYRIMIDINE 2,4-'DIONE
  • a mixture of 220 cc. of ethanol, 21 g. of sodium methylate and 18.5 g. of N-(2'-tetrahydropyranyl) N (Z-ethoxycarbonyl) l cyclopentenylurea keeps at reflux temperature for ten minutes, cools the reaction mixture, concentrates it to dryness under reduced pressure, dissolves the residue in water, acidifies the aqueous solution with a 22 B.
  • Ekapersol S is the trade name of a sodium dinaphthylmethanedisulfonate.
  • Brecolane N.V.A. is the trade name of a sodium alkylnaphthalenesulfonate.
  • compound I possesses herbicidal properties.
  • the herbicidal activity of the compound I was evidenced by tests on plants representative of the great hotanical families such as oats, wheat, maize, foxtail grass (Gramineae), beet (Chenopodiaceae), chrysanthemum (Compositae), bean, clover (Papilionaceae), flax (Linaceae) and mustard (Cruciferae).
  • the earthy mixture used was composed of 10 volumes of earth, 10 volumes of river sand and 2 volumes of peat.
  • the product to be studied was applied twenty-four hours after sowing, under standard conditions, by means of a microsprayer, at doses corresponding to 10, 5, 2.5 and 1.25 kg./ha. and at a diluent corresponding to 560 l./ha.
  • the efficacy of the tested compound was checked by weighing the seedlings twenty-one days after treatment, in comparison with non-treated controls.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A SUBSTITUTED PYRIMIDINE, OF FORMULA I;

3-(TETRAHYDROPYRAN-2-YL)-6,7-DIHYDRO-5H-CYCLOPENTA(D)-

PYRIMIDINE-2(1H),4(3H)-DIONE

COMPOSITIONS CONTAINING THE SAME, PROCESS AND METHOD. THE COMPOUND I POSSESS PESTICIDAL, PARTICULARLY HERBICIDAL PROPERTIES.

Description

United States Patent Oflice 3,658,819 3-(2'-TETRAHYDROPYRANYL) 1,2,3,4,6,7-HEXA- HYDRO 5H CYCLOPENTAPYRIMIDINE-2,4- DIONE Daniel Bertin, Montrouge, and Jacques Perronnet and Andre Teche, Paris, France, assignors to Roussel- UCLAF, Paris, France No Drawing. Filed Jan. 16, 1970, Ser. No. 3,499 Claims priority, applicsggtiialfrance, Jan. 29, 1969,
Int. Cl. C07d 51/18, 7/14 US. Cl. 260-260 1 Claim ABSTRACT OF THE DISCLOSURE A substituted pyrimidine, of Formula I:
compositions containing the same, process and method.
The compound I possesses pesticidal, particularly herbicidal properties.
THE PRIOR ART French Pat. No. 1,270,771 describes herbicidal comounds of the formula:
where X is oxygen or sulfur, and the substituents R to R are covalent radicals.
OBJECTS OF THE INVENTION The compound of Formula I is endowed with remarkable pesticidal, specifically herbicidal properties which 3,658,819 Patented Apr. 25, 1972 make it useful in agriculture for controlling harmful organisms and more particularly for controlling the growth of weeds.
The process of the invention for the preparation of compound I comprises condensing 2-ethoxycarbonyl-cyclopentanone with N-(Z-tetrahydropyranyl)-urea in the presence of a proton donor, cyclizing the resulting N-(2-tetrahydropyranyl)-N-(2-ethoxycarbonyl) 1 cyclopentenylurea in the presence of a basic agent, and recovering the desired compound of Formula I.
Preferably, the proton donor is an acid, such as phos phoric acid, acetic acid, pyruvic acid, an ammonium salt such as ammonium chloride, or an acidic ion exchange resin.
The condensation of 2-ethoxycarbonyl-cyclopentanone with N-(Z-tetrahydropyranyl)-urea is preferably carried out in an organic polar solvent such as acetonitrile, nitrobenzene, nitromethane or dimethylsulfoxide.
The basic agent used in the cyclization reaction is preferably an alkali-metal alcoholate such as an alkali-metal alkoxide, e.g. sodium or potassium, methylate or ethylate, and the cyclization reaction is performed in the presence of an alcohol such as ethanol; or the basic agent is an alkali-metal amide such as sodium or potassium amide, or an alkali-metal hydride, such as sodium hydride, and the cyclization reaction is performed in an ether such as tetrahydrofuran, ethyl ether, or in dimethylformamide.
The preparation of 2-'ethoxycarbonyl-cyclopentanone and of N-(Z-tetrahydropyranyl)-urea are described by way of exemplification in the experimental part of the description.
The pesticidal, specifically herbicidal compositions of the invention, generally, contain from 10 to by weight of the compound I as active ingredient, and an adjuvant. These compositions may also contain one or several other pesticidal agents or one or several products influencing plant growth.
Preferably, the compositions of the invention contain from 10 to 50% by weight of active ingredient.
The compositions of the invention can be in the form of powders, granules, suspensions, emulsions, solutions containing specifically, in addition to the active principles, an adjuvant, such as a surface-active cationic, anionic or non-ionic agent, such as aryl or alkylarylsulfonates, inert powders such as talc, clays, silicates, colloidal kaolin, kieselguhr, synthetic silica, and the like, and/or a vehicle such as water, alcohol, hydrocarbons or other organic solvents, a mineral, animal or vegetable oil, etc.
The invention likewise relates to a method of pesticidal control.
Said method is more particularly a method of controlling the growth of harmful organisms and specifically of weeds, which comprises contacting the harmful organisms, particularly the weeds and/or their seeds, with a pesticidal amount, particularly a herbicidal amount of the compound I. The compound of Formula I is preferably applied in the form of the compositions described above.
The compositions of the invention are applied at doses sufiicient to exert their pesticidal, specifically herbicidal activities. The doses of active ingredient to be applied may vary as a function of the weeds, the nature of the ground and the weather conditions.
The invention also relates to N-(2-tetrahydropyranyl)- N'- .(2-ethoxycarbonyl)-1-cyclopentenyl-urea which is an intermediate in the process described above.
The following examples illustrate the invention without however limiting it.
PREPARATION I 2-ethoxycarbonyl-cyclopentanone Into 500 cc. of dimethylsulfoxide, one introduces, under an atmosphere of nitrogen, 25 g. of a 50% sodium hydride suspension in Vaseline oil, then a solution of 101 g. of ethyl adipate, in 101 cc. of dimethylsulfoxide, is added over a period of about one hour. One agitates the reaction mixture at 25 C. for two hours, heats it to 100 C. and keeps it at that temperature for one hour. One cools the reaction mixture, pours it into a mixture of water and ice, acidifies to pH=2 with a 22 B. aqueous solution of hydrochloric acid, extracts the aqueous phase with ethyl acetate, washes the organic extracts with water, dries them, concent rates them to dryness under reduced pressure, redistills the residue in vacuo and obtains 47.5 g. of 2- ethoxycarbonyl-cyclopentanone, B.P. mm 132 C.
Analysis.-Calcd. for C H O (percent): molecular weight==l56.18. C, 61.52; H, 7.75. Found (percent): C, 61.6; H, 7.7.
This compound is identical to that described by P. S. Pinkney, Organic Synth, XVII, p. 31 (1937 edition).
PREPARATION II N-(2-tetrahydropyrany1)-urea One takes to reflux a mixture of 120 g. of urea, 500 cc. of benzene, 170 g. of 2,3-dihydropyran and 5 g. of p-tluenesulfonic acid, keeps at reflux temperature for one hour, cools the reaction mixture to 20 C., isolates the precipitate thus formed by suction-filtering crystallizes it from ethanol and obtains 80 g. of N-(Z-tetrahydropyranyl)-urea; M.P.-=188 C.
A sample of this product is purified by crystallization from ethanol; M.P.= 191 C.
Analysis.-Calcd. for C H N (percent): molecular weight=1444.18. C, 49.97; H, 8.39; N, 19.44. Found (percent): C, 50.0; H, 8.4; N, 19.3.
This compound is identical to that described by SM. Amir et al. Nature 192, 1069 (1961).
EXAMPLE 1 STAGE A: N- (2'-TETRAHYDROPYRANYL) -N' (2-ETHOX- YCARBONYL) -1-CYCLOPENTENYL-UREA One heats to 70 C. a mixture of 37 g. of Z-ethoxycarbonyl-cyclopentanone, 300 cc. of acetonitrile, 100 cc. of benzene and cc. of phosphoric acid, inttroduces thereto, over a period of about one hour, 50 g. of N-(Z-tetrahydropyranyl)-urea, takes the reaction mixture to reflux, keeps it at reflux for two hours, while removing the water formed during the reaction by azeotropic distillation and simultaneously adding benzene to keep the volume constant. One then adds 25 g. of N-(Z-tetrahydropyranyl)-urea, continues distillation with addition of benzene for two hours, again adds 25 g. of N-(Z-tetrahydropyranyl)-urea and keeps at reflux with distillation and addition of benzene for two more hours. One cools the reaction mixture and concentrates it to dryness under reduced pressure. The residue is purified by chromatography on silica gel while eluting with a mixture of benzene and ethyl acetate (7-3) and one obtains 6 g. of-N-(2-tetrahydropyranyl)-N'-(2 ethoxycarbonyl) l cyclopentenylurea; M.P.=116 C.
LR. Spectrum (in chloroform) Absorptions at:
3436 cm. (associated NH):
1709, 1661, 1625 cm." (carbonyl groups and double bond C=C);
1520 cm.- (HN--).
As far as is known, this compound is not described in the literature.
STAGE B: 3(2-TETRAHYDROPYRANYL)-1,2,3,4,6,7 5H- CYCLOPENTAPYRIMIDINE 2,4-'DIONE One takes to reflux a mixture of 220 cc. of ethanol, 21 g. of sodium methylate and 18.5 g. of N-(2'-tetrahydropyranyl) N (Z-ethoxycarbonyl) l cyclopentenylurea, keeps at reflux temperature for ten minutes, cools the reaction mixture, concentrates it to dryness under reduced pressure, dissolves the residue in water, acidifies the aqueous solution with a 22 B. aqueous solution of hydrochloric acid, isolates the precipitate thus formed by suction-filtering, dries it and obtains 11.5 g. of 3-(2'- tetrahydropyranyl)-l,2,3,4,6,7-hexahydro SH-cyclopentapyrimidine 2,4-dione; M.P.=269 C., which remained unchanged after recrystallization from ethanol.
Analysis.Calcd. for C H N O (percent): molecular weight=236.25. C, 61.00; H, 6.82; N, 11.86. Found (percent): C, 61.0; H, 6.7; N, 12.0.
As far as is known, this compound is not described in this literature.
EXAMPLE 2 Wettable powder composition Ekapersol S 15 Brecolane N.V.A. 0.5 Synthetic silica 34.5 Colloidal kaolin 25 The composition thus obtained may be applied with the usual spraying devices after dilution.
Ekapersol S is the trade name of a sodium dinaphthylmethanedisulfonate.
Brecolane N.V.A. is the trade name of a sodium alkylnaphthalenesulfonate.
As indicated above, compound I possesses herbicidal properties.
The herbicidal activity of the compound I, was evidenced by tests on plants representative of the great hotanical families such as oats, wheat, maize, foxtail grass (Gramineae), beet (Chenopodiaceae), chrysanthemum (Compositae), bean, clover (Papilionaceae), flax (Linaceae) and mustard (Cruciferae).
Details of the herbicidal tests are given below. Study of the pre-emergence herbicidal properties of the compound of Formula I: The 9 plants used (oats, beet, wheat, Chrysanthemum, flax, maize, mustard, clover and foxtail grass) were cultivated in a culture vessel (23 x 14 x 4 cm.), with a double-bottom for watering from below. The 9 plants were sown, at the rate of 20 seeds each, in a single vessel, and four of such vessels were used for each dose of compound I. The conditions of cultivation were the following:
Temperature: 20 C.i2 C.; relative humidity: about 60%; lighting by fluorescent tubes (daylight-l-brilliant white type): from six am. to ten pm. every day. The earthy mixture used was composed of 10 volumes of earth, 10 volumes of river sand and 2 volumes of peat.
The product to be studied was applied twenty-four hours after sowing, under standard conditions, by means of a microsprayer, at doses corresponding to 10, 5, 2.5 and 1.25 kg./ha. and at a diluent corresponding to 560 l./ha.
The efficacy of the tested compound was checked by weighing the seedlings twenty-one days after treatment, in comparison with non-treated controls.
The following table expresses the results obtained in pre-emergence treatment for compound I.
The results are expressed in percentage of reduction Various modifications of the process, compositions of the vegetation P: and method of the invention may be made without deweight of the control seedlings-weight of the treated seedlings Partmg P the spun and Scope thereof- P= x 100 We claim:
weghtthemmlseedlmgs 5 1. 3-(2-tetrahydropyranyl)-1,2,3,4,6,7-hexahydro-5H- Percent cyclopentapyrimidine 2,4-di0ne, of the formula:
s 2.5 1. kgJha. kgJha. kgJha. kgJha.
0 72 N as 10 10 N O 100 0 0 46 97 15 References Cited CONCLUSION UNITED STATES PATENTS Compound I is endowed with a good pre-emergence 3360521 12/1967 Soboczenski 260-260 herbicidal activity on most of the dicotyledons and on foxtail grass, while it has only a slight activity on wheat 2 ALEX MAZEL Primary Exammer and on maize. A. M. T. TIGHE, Assistant Examiner The post-emergence herbicidal activity of compound I was evidenced on the same plants, by tests analogous to that described for pre-emergence activity, but the treat- 260-3453, 468 R; 71-92 ment is effected twenty-one days after sowing. 25
US3499A 1969-01-21 1970-01-16 3-(2'-tetrahydropyranyl) - 1 2 3 4 6 7-hexahydro - 5h - cyclopentapyrimidine-2 4-dione Expired - Lifetime US3658819A (en)

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US00187914A Expired - Lifetime US3785800A (en) 1969-01-21 1971-10-08 New substituted pyrimidine

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CA (1) CA966129A (en)
CH (1) CH522674A (en)
DE (1) DE2002586A1 (en)
ES (1) ES375689A1 (en)
FR (1) FR2029250A5 (en)
GB (2) GB1255891A (en)
IL (1) IL33697A (en)
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NL (1) NL7000628A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0045078A1 (en) * 1980-07-28 1982-02-03 Hoechst-Roussel Pharmaceuticals Incorporated (1,2-Benzisoxazol)phenoxyacetic acids and related compounds
WO2009140127A3 (en) * 2008-05-13 2010-01-28 Boehringer Ingelheim International Gmbh SYNTHESIS OF DIHYDROTHIENO[3,2-d]PYRIMIDINE DIOLS AND SIMILAR PYRIMIDINE DIOLS

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2590767A1 (en) * 1985-12-02 1987-06-05 Soyez Jean Louis Novel use of a substituted uracile and its associations as a selective herbicide in maize crops

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0045078A1 (en) * 1980-07-28 1982-02-03 Hoechst-Roussel Pharmaceuticals Incorporated (1,2-Benzisoxazol)phenoxyacetic acids and related compounds
WO2009140127A3 (en) * 2008-05-13 2010-01-28 Boehringer Ingelheim International Gmbh SYNTHESIS OF DIHYDROTHIENO[3,2-d]PYRIMIDINE DIOLS AND SIMILAR PYRIMIDINE DIOLS
CN102026984A (en) * 2008-05-13 2011-04-20 贝林格尔.英格海姆国际有限公司 Synthesis of dihydrothieno[3,2-d]pyrimidine diols and similar pyrimidine diols
US20110130563A1 (en) * 2008-05-13 2011-06-02 Boehringer Ingelheim International Gmbh Synthesis if dihydrothieno[3,2-d]pyrimidine diols
US8471010B2 (en) 2008-05-13 2013-06-25 Boehringer Ingelheim International Gmbh Synthesis of dihydrothieno[3,2-d]pyrimidine diols
CN102026984B (en) * 2008-05-13 2013-12-25 贝林格尔.英格海姆国际有限公司 Synthesis of dihydrothieno[3,2-d]pyrimidine diols and similar pyrimidine diols
TWI421254B (en) * 2008-05-13 2014-01-01 Boehringer Ingelheim Int Synthesis of dihydrothieno[3,2-d]pyrimidine diols and similar pyrimidine diols
AU2009246686B2 (en) * 2008-05-13 2014-02-13 Boehringer Ingelheim International Gmbh Synthesis of dihydrothieno[3,2-d] pyrimidine diols and similar pyrimidine diols
EA019735B1 (en) * 2008-05-13 2014-05-30 Бёрингер Ингельхайм Интернациональ Гмбх SYNTHESIS OF DIHYDROTHIENO[3,2-d]PYRIMIDINE DIOLS AND SIMILAR PYRIMIDINE DIOLS

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FR2029250A5 (en) 1970-10-16
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NL7000628A (en) 1970-07-23
AT307142B (en) 1973-05-10
DE2002586A1 (en) 1970-08-27
GB1255892A (en) 1971-12-01
AT297702B (en) 1972-04-10
LU60208A1 (en) 1970-03-20
US3785800A (en) 1974-01-15
ES375689A1 (en) 1972-05-16
CA966129A (en) 1975-04-15
CH522674A (en) 1972-06-30
GB1255891A (en) 1971-12-01

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